Tert-Butyl nitrite → 8,9-Dimethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Participants

Reaction Conditions

Reaction Steps

2-Amino-4,5-dimethyl-N-quinolin-8-yl-benzenesulfonamide (Intermediate 164) (100 mg, 0.31 mmol) was suspended in acetic acid: THF (1:1) (2 ml) and cooled to 0° C. Tert-butylnitrite (54 μl, 0.46 mmol) was added and the reaction was slowly warmed to 5° C. over 3 h. The reaction was quenched with water (4 ml) and the resulting solution was concentrated in vacuo. The residue was dissolved in EtOAc (10 ml) and washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM as the eluent to give the title compound (7 mg, 7%).

Provenance & Evidence